ethyl (E)-3-(2R)-6-oxo-5-phenylsulfonyltetrahydro-2H-pyran-2-yl-2-propenyl carbonate

Base Information

Chemical Name:ethyl (E)-3-(2R)-6-oxo-5-phenylsulfonyltetrahydro-2H-pyran-2-yl-2-propenyl carbonate
CAS No.:669000-30-0
Molecular Formula:C₁₇H₂₀O₇S
Molecular Weight:368.408
Hs Code.:

Synonyms:ethyl (E)-3-(2R)-6-oxo-5-phenylsulfonyltetrahydro-2H-pyran-2-yl-2-propenyl carbonate

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Chemical Property of ethyl (E)-3-(2R)-6-oxo-5-phenylsulfonyltetrahydro-2H-pyran-2-yl-2-propenyl carbonate

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Technology Process of ethyl (E)-3-(2R)-6-oxo-5-phenylsulfonyltetrahydro-2H-pyran-2-yl-2-propenyl carbonate

There total 7 articles about ethyl (E)-3-(2R)-6-oxo-5-phenylsulfonyltetrahydro-2H-pyran-2-yl-2-propenyl carbonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

: 541-41-3
chloroformic acid ethyl ester

: 669000-40-2
(R)-3-Benzenesulfonyl-6-((E)-3-hydroxy-propenyl)-tetrahydro-pyran-2-one

: 669000-30-0
ethyl (E)-3-(2R)-6-oxo-5-phenylsulfonyltetrahydro-2H-pyran-2-yl-2-propenyl carbonate

Guidance literature:: With pyridine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/ol0363366

Reference yield:

: 157918-29-1
methyl (2E,4R)-4-<<(tert-butyl)dimethylsilyl>oxy>-6-hydroxyhex-2-eneoate

: 669000-30-0
ethyl (E)-3-(2R)-6-oxo-5-phenylsulfonyltetrahydro-2H-pyran-2-yl-2-propenyl carbonate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 99 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

2.1: 96 percent / DIBAL / CH₂Cl₂; toluene / -78 - -40 °C

3.1: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / 20 °C

4.1: sodium hydride / dimethylformamide; various solvent(s) / 2 h

4.2: 87 percent / dimethylformamide; various solvent(s) / 15 h / Heating

5.1: 92 percent / camphorsulfonic acid / methanol / 5 h

6.1: 80 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 2 h / 20 °C

7.1: 95 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

With pyridine; dmap; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/ol0363366

Reference yield:

: 669000-39-9
(E)-(R)-2-Benzenesulfonyl-5,8-dihydroxy-oct-6-enoic acid methyl ester

: 669000-30-0
ethyl (E)-3-(2R)-6-oxo-5-phenylsulfonyltetrahydro-2H-pyran-2-yl-2-propenyl carbonate

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 2 h / 20 °C

2: 95 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

With pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetonitrile;
DOI:10.1021/ol0363366